Control of Stereoselectivity in Diverse Hapalindole Metabolites is Mediated by Cofactor‐Induced Combinatorial Pairing of Stig Cyclases | Zendy

Li Shasha | Zendy; Newmister Sean A. | Zendy; Lowell Andrew N. | Zendy; Zi Jiachen | Zendy; Chappell Callie R. | Zendy; Yu Fengan | Zendy; Hohlman Robert M. | Zendy; Orjala Jimmy | Zendy; Williams Robert M. | Zendy; Sherman David H. | Zendy

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Control of Stereoselectivity in Diverse Hapalindole Metabolites is Mediated by Cofactor‐Induced Combinatorial Pairing of Stig Cyclases

Author(s) -

Li Shasha,

Newmister Sean A.,

Lowell Andrew N.,

Zi Jiachen,

Chappell Callie R.,

Yu Fengan,

Hohlman Robert M.,

Orjala Jimmy,

Williams Robert M.,

Sherman David H.

Publication year - 2020

Publication title -

angewandte chemie

Language(s) - English

Resource type - Journals

eISSN - 1521-3757

pISSN - 0044-8249

DOI - 10.1002/ange.201913686

Subject(s) - stereospecificity , chemistry , stereochemistry , stereoselectivity , electrophile , pairing , cofactor , combinatorial chemistry , biochemistry , enzyme , catalysis , physics , superconductivity , quantum mechanics

Stereospecific polycyclic core formation of hapalindoles and fischerindoles is controlled by Stig cyclases through a three‐step cascade involving Cope rearrangement, 6‐ exo ‐trig cyclization, and a final electrophilic aromatic substitution. Reported here is a comprehensive study of all currently annotated Stig cyclases, revealing that these proteins can assemble into heteromeric complexes, induced by Ca 2+ , to cooperatively control the stereochemistry of hapalindole natural products.

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